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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
(E)-4-Chloro-N-[(E)-2-methyl-3-phenyl-allyl-idene]aniline
This study characterizes a Schiff base compound, C(16)H(14)ClN, detailing its specific E configurations and molecular geometry. The crystal structure reveals intermolecular hydrogen bonds influencing molecular stacking.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Schiff bases are versatile organic compounds with diverse applications.
- Understanding the three-dimensional structure of organic molecules is crucial for predicting their properties and reactivity.
- Intermolecular interactions, such as hydrogen bonding, play a significant role in crystal packing and material properties.
Purpose of the Study:
- To elucidate the precise molecular structure and stereochemistry of the Schiff base compound C(16)H(14)ClN.
- To investigate the dihedral angles and planarity of the core structural elements.
- To identify and describe the intermolecular interactions present in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the crystal structure.
- Analysis of bond configurations (C=C and C=N) and dihedral angles.
- Identification of hydrogen bonding networks (C-H⋯Cl and C-H⋯N).
Main Results:
- The compound C(16)H(14)ClN exhibits E configurations for both C=C and C=N bonds.
- The dihedral angle between the two aromatic rings is 53.27(4)°.
- Weak C-H⋯Cl and C-H⋯N hydrogen bonds facilitate molecular stacking along the a-axis.
Conclusions:
- The study provides a detailed structural characterization of the title Schiff base.
- The observed molecular geometry and hydrogen bonding patterns offer insights into its solid-state behavior.
- This structural data can inform future studies on the synthesis and application of related Schiff base derivatives.
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